Parthenolide

Parthenolide is a sesquiterpene lactone of the germacranolide class which occurs naturally in the plant feverfew (Tanacetum parthenium), after which it is named, and in the closely related tansy (Tanacetum vulgare).^[1] It is found in highest concentration in the flowers and fruit. Parthenolide's molecular structure depiction is often incorrect regarding the stereochemistry of the epoxide, although X-ray single crystal structures are available.^[2][3]

Quick facts Names, Identifiers ...

Parthenolide

Names
IUPAC name (1aR,4E,7aS,10aS,10bR)-2,3,6,7,7a,8,10a,10b-octahydro-1a,5-dimethyl-8-methylene-oxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one
Identifiers
CAS Number	20554-84-1 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL540445 N
ChemSpider	20126246 N
ECHA InfoCard	100.220.558
PubChem CID	5420805
RTECS number	LY4220000
UNII	2RDB26I5ZB N
CompTox Dashboard (EPA)	DTXSID2040579
InChI InChI=1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5+/t11-,12-,13-,15+/m0/s1 N Key: KTEXNACQROZXEV-SLXBATTESA-N N Key: KTEXNACQROZXEV-SLXBATTEBY InChI=1/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5+/t11-,12-,13-,15+/m0/s1
SMILES C/C/1=C\CC[C@@]2([C@@H](O2)[C@@H]3[C@@H](CC1)C(=C)C(=O)O3)C
Properties
Chemical formula	C15H20O3
Molar mass	248.322 g·mol−1
Melting point	113 to 115 °C (235 to 239 °F; 386 to 388 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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Lack of solubility in water and bioavailability limits the potential of parthenolide as a drug.